Blue cotton-dye.



hurrah s rapes Parana carton.

HEINRICH JORDAN :ANID WILHELM GERMANY, ASSIGNORS TO FARBENFABR-IKEN VORM. FR-IEDR.

NEELMEIER, or tsv'nnxusnu, NEAR concern,- BAYER & 00., or

ELBERFELJD, GERMANYA CORPORATION OF GERMANY.

BLUE COTTON-DYE.

No Drawing. a

- which the following is a specification.

The present invention relates tothe manufacture of new azo dyestuffs capable of dyeing cotton in from reddish-blue to greenishreducing; the nitro group,

blue shades which by an after treatment with diazotized para-nitranilin or other suitable diazo compounds are rendered fast to washing. The shades thus obtained can be easily discharged with hydrosulfite to a pure white. The new dyes having most probably the formula:

in Which-R means an aromatic nucleus, and X- the radical of an oxy-naphthalene sulfonic acid, are after being dried and pulverized in the shape of their alkaline salts dark powders soluble in water. They yield upon reduction with stannous c'hlorid and hydrochloric acid 2 amino 1.8 dioxynaphthalene-sl-sulfonic acid, a para-phenylenediamin compound a diamiu and an aminonaphthol sult'onic acid.

The process for V consists in combining diazotized acidyl-paraphenylenediamins or para-nitranilin their homologues or substitution products with a suitable middle component capable of being diazotizcd after combination, rediazotizing the monoazo dye obtained, combining it with a naphthol sultonic acid, eliminating the acidyl radical from the acidyl compounds or diazotizing the amino compounds thus produced and combining them with 1.8-dioxynaphthalene-4- sulfonic acid.

In order to illustrate the new process more fully the following examples are given, the

parts being by Weight:

Example 1.: 244.5 parts of 2-oxalylamino- 4-chloro-5-amino-l-anisol (CuHazOCFI'mNFLCQC-OOHzGl:NH==1:21425) Y are dissolved in 7000 parts of water contain Specification of Letters Patent.

NEELMIEIER, doctors of phi-' trite.

producing the new dyes Patented July 16, 1912.

Applicatiouiiled September 1, 1911. Serial No. 647,252.

ing parts of sodium carbonate, 280 parts of hydrochloric acid of 19 B. are added and the mixture after being cooled to1.0 C. is diazotized with 69 parts of sodium ni- The resulting diazo compound is introduced into a solution of 245 parts of 1- naphthylamin-(i-sulfonate (if sodium containing 250 parts of a 100 er cent. sodium acetate. The combination is complete after some minutes. After acidulation with hydrochloric acid the aininoazo compound is diazotized at 10 C. with 69 parts of sodium nitrite. The mixture is stirred for one hour and the diazo compound is thenintroduced into an aqueous solution cooled to. 0C. of 246 parts of Q-naph'thol-7-sulfonatc of sodium in water containing 550 palrtsof carbon ate of sodium. The dye is recipitated with common salt and filtered oii It is then dissolved in 7000 parts of boiling water and the solution in order to eliminate the oxalylgroup is heated to boiling for 10 minutes with 1500 parts of a 80 per cent. caustic soda lye, then cooled to 70"- (1, and the excess of NaOH neutralized with acid. The dye is filtered off and is then well mixed with 7000 parts of cold water, acidulated with 250 parts of hydrochloric acid and diazotized with 00 parts of sodium nitrite. The diazotation is complete after 4-5 hours stirring and the diazo compound is then added to a cooled solution of 262 parts of the sodium salt of 1.S-dioxynapht-halene-issulfonic 'acid con-- taining 800 parts of sodium acetate and a small quantity of acetic acid to render the solution slightly acid. It is stirred for half an hour and the mixture is then rendered weakly alkaline with carbonate of soda. The dye is filtered ofi. and dried. It'dyes cotton blue. The dye has most probably the formula: 1

It is a dark powder soluble in water with a blue coloration, soluble in concentrated sulfuric acid with an olive coloration; yielding upon reduction with stannous chlorl'd and hydrochloric acid 2.5diamino-4-chloro'- are dissolv d in 2000 parts of water containing 170 parts of hydrochloric acid of 19 B6. The solution is run into a mixture of i 130 parts of hydrochloric acid and ice and is diazotized at from 5 to 10 C. The combination with 1 naphthylamin 6 sulfonic acid and then with 2-naphthol-7-sulfonic acid is carried out as described in Example The disazo dye thus obtainedis filtered oil.

7 It is then well mixed up with 7000 parts of water, the mixture is heated to 4-0-50 G. and reduced by means of 400 parts of crystallized sodium sulfid. stirring for 2 hours. the dye is salted out,

' filtered oil and YrflSi'lCftWltll a solution of 2 oxalylamino- 4 methyl-fi-am1nol-aniscl 2-acet-ylam1no-5-amino-l l-dlchlorobenzene;

common salt. It is then made into a paste with 7000 parts of water, 300 parts. of hy-,

drochloric acid are added and the azo dye diazotized with 69 parts of sodium nitrite. The further combination with the -1.8-di- -oxynaphthalenel-sulfonic acid is carried out as it is described in Ilxamplel. Other first componentsmay be used c. g. monooxalyl-para-phenylenediamin, Q-oxalylamino-5-amino-para-Xylol likewise other middle components 6.

l-naphthylamin, l-naphthylamin-7sulfonic acid, m'fta-toludin, Xylidin, crcsidin and other naphthol sulfonic acids 6. g. l.3, 1.-i, 1.5-,- 1.8-, 2.5-, 270-, 2.8-naphthol sulfonic acids or 1.3.0, 1.3.7-, 1.3.8-, 1.4.7-, 1.4.8

1.5.1, 2.3a, 2.4a, 2.5.7:,-2 .6;8-naphthol-disulfonic acids, etc, may be used.

After \Ve claim: l. The herein described new azo dyestufis having most probably thefo-rmula:

fonic acid, which are after being dried and pulverized in the shape of their alkaline salts dark powders soluble in water; ylelding upon reduction with stannous chlorld and hydrochloric acid 2-amin'o-1.8-dioxynaphthalene4-sulfonic acid, a para-phenylenediamin compound, a diamin and an aminonaphthol sulfonic acid; dyeing cotton in from reddish-blue to greenishrblue shades whichby an after treatment with diazotized para-nitranilin or other suitable diazo compounds are rendered fast-,to washing and which can be easily discharged with hydrosulfite to a pure white, substantially as described.

The herein described new azo dyestutt having most probably the formula: I

OH OH III 1 S oan which is a dark powder soluble in water with a blue coloration and soluble in concentrated sulfuric acid with an olive coloration; yielding upon reduction with stannous chlorid and hydrochloric acid 2.5-diaminol-chloro-l-anisol, 1.4-naphthylenedianiin-(isulfonic acid, l-amino-Q-naphthol-T-sulfrmic acid and Q-amino-LS-dioxynaphthalene-etsulfonic acid; dyeing cotton in clear blue shades which by an after treatment with I diazotized para-nitranilin are rendered fast to washing and whlch can be easily discharged with hydrosulfite to a pure white, substantially as described.

In testimony whereof we have hereunto set our hands in the presence of two subscribing witnesses.

HEINRICH JORDAN.

I'L. s] l-VILHELh I NEELMETER. [Lt s] Witnesses:

jCI-IAs. J. Wluon'r, L. NUFER.

Copies of this patent may be obtained for five cents each, by addressing the Commissioner of Patents,

Washington, D. G. 

